Ethyl fluoroacetate
[CAS# 459-72-3]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Ethyl fluoroacetate
• Molecular Formula: C₄H₇FO₂
• Molecular Weight: 106.10
• CAS Registry Number: 459-72-3
• EC Number: 207-297-8
• SMILES: CCOC(=O)CF

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*, 1.093 g/mL (Expl.)
• Index of Refraction: 1.354, Calc.^*,1.375 (Expl.)
• Boiling Point: 118.0±8.0 °C (760 mmHg), Calc.^*, 119.6 °C (Expl.)
• Flash Point: 30.0 °C, Calc.^*, 30 °C (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS06;GHS09 Danger
• Risk Statements: H226-H300-H310-H330-H400
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P262-P264-P270-P271-P273-P280-P284-P301+P316-P302+P352-P303+P361+P353-P304+P340-P316-P320-P321-P330-P361+P364-P370+P378-P391-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	2	H300
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	2	H310
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	1	H310
Acute toxicity	Acute Tox.	1	H330

• Transport Information: UN 2929

Discovery and Applications

Ethyl fluoroacetate is an organic compound with the molecular formula C4H7FO2. It is a colorless liquid with a pungent odor, and it is commonly used as a chemical intermediate in the synthesis of various compounds. Ethyl fluoroacetate is primarily known for its applications in the synthesis of pharmaceuticals and agrochemicals, and it has significant importance in organic chemistry due to its ability to introduce fluorine into organic molecules.

Ethyl fluoroacetate was first synthesized in the early 20th century, with its primary role in chemical synthesis being identified over time. The compound contains both a fluoroacetate group (-CO2CH2F) and an ethyl ester group (-C2H5), making it a versatile intermediate for the creation of more complex chemical structures. The presence of the fluorine atom in the structure of ethyl fluoroacetate plays a crucial role in its chemical properties, such as increasing its reactivity and altering the metabolic behavior of the compounds it is used to synthesize.

One of the key applications of ethyl fluoroacetate is in the pharmaceutical industry, where it is used as an intermediate for the synthesis of various bioactive molecules. Fluorine substitution often leads to improved bioactivity, stability, and lipophilicity of pharmaceutical compounds, making ethyl fluoroacetate valuable in drug development. In particular, its use in the preparation of fluorinated drugs, which can enhance their pharmacokinetic properties, is of significant importance.

In agrochemicals, ethyl fluoroacetate has been utilized as a precursor in the synthesis of certain herbicides and pesticides. The ability to incorporate fluorine into organic molecules makes it a useful building block for designing chemicals with specific biological activity. Its role in agrochemical production has led to its application in formulations that target plant pathogens or weeds.

Additionally, ethyl fluoroacetate has been employed in laboratory research, particularly in studies related to the synthesis of fluorinated organic compounds. Researchers use it as a reagent to introduce fluorine atoms into molecular structures, contributing to the development of new materials or chemicals with unique properties.

While ethyl fluoroacetate has useful applications, it is important to note that it is highly toxic. It can act as a potent inhibitor of enzymes in biological systems, particularly in the central nervous system, which contributes to its toxicological profile. As a result, handling ethyl fluoroacetate requires caution and appropriate safety measures.

Overall, ethyl fluoroacetate is an important compound in organic chemistry, particularly for the synthesis of fluorinated pharmaceuticals, agrochemicals, and other organic molecules. Its ability to introduce fluorine into complex molecules enhances the properties and reactivity of the final products, making it a valuable tool in chemical synthesis.

References

2003. Gamma-fluorinated analogues of glutamic acid and glutamine. Amino Acids, 24(4).
DOI: 10.1007/s00726-002-0410-9

2006. Determination of fluoroacetic acid in water and biological samples by GC-FID and GC-MS in combination with solid-phase microextraction. Analytical and Bioanalytical Chemistry, 386(6).
DOI: 10.1007/s00216-006-0713-x

2014. Fluorine-Containing Diazines in Medicinal Chemistry and Agrochemistry. Fluorine in Heterocyclic Chemistry Volume 2.
DOI: 10.1007/978-3-319-04435-4_7